# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z
_database_code_depnum_ccdc_archive 'CCDC 1819863'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2018-08-04 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 B F5 N O P S'
_chemical_formula_weight         476.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5464(2)
_cell_length_b                   17.3658(6)
_cell_length_c                   21.0198(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.3700(10)
_cell_angle_gamma                90.00
_cell_volume                     2374.85(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7204
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.44

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9137
_exptl_absorpt_correction_T_max  0.9320
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27898
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.01
_reflns_number_total             8322
_reflns_number_gt                7464
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0468P)²+0.3726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8322
_refine_ls_number_parameters     583
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.06189(11) 1.09824(4) 0.47919(3) 0.02959(16) Uani 1 1 d . . .
P2 P 0.15534(12) 0.94145(4) 0.29996(3) 0.02735(17) Uani 1 1 d . . .
B2 B -0.1358(6) 0.9520(3) 0.2840(2) 0.0450(10) Uani 1 1 d . . .
H2C H -0.182(6) 0.894(2) 0.2630(18) 0.064(11) Uiso 1 1 d . . .
H2D H -0.146(6) 0.996(2) 0.2471(19) 0.065(11) Uiso 1 1 d . . .
H2B H -0.190(6) 0.967(2) 0.322(2) 0.062(12) Uiso 1 1 d . . .
F6 F 0.5632(3) 1.14275(9) 0.40400(9) 0.0399(4) Uani 1 1 d . . .
F7 F 0.6658(3) 1.29286(11) 0.40480(9) 0.0483(5) Uani 1 1 d . . .
F8 F 0.3809(3) 1.39995(10) 0.36248(10) 0.0551(5) Uani 1 1 d . . .
F9 F -0.0083(3) 1.35596(11) 0.31841(10) 0.0548(5) Uani 1 1 d . . .
F10 F -0.1077(3) 1.20610(10) 0.31468(9) 0.0432(4) Uani 1 1 d . . .
O2 O 0.2131(4) 1.14908(12) 0.51557(10) 0.0453(6) Uani 1 1 d . . .
N2 N 0.1791(4) 1.04940(13) 0.42378(10) 0.0267(5) Uani 1 1 d . . .
C22 C 0.2433(4) 0.87077(15) 0.35974(13) 0.0257(6) Uani 1 1 d . . .
C23 C 0.4518(5) 0.85886(17) 0.37954(14) 0.0337(7) Uani 1 1 d . . .
H23A H 0.5523 0.8901 0.3628 0.040 Uiso 1 1 calc R . .
C24 C 0.5116(5) 0.80219(18) 0.42318(15) 0.0385(7) Uani 1 1 d . . .
H24A H 0.6534 0.7943 0.4366 0.046 Uiso 1 1 calc R . .
C25 C 0.3640(6) 0.75612(18) 0.44783(15) 0.0400(8) Uani 1 1 d . . .
H25A H 0.4055 0.7162 0.4774 0.048 Uiso 1 1 calc R . .
C26 C 0.1592(6) 0.76857(17) 0.42927(15) 0.0410(8) Uani 1 1 d . . .
H26A H 0.0587 0.7381 0.4468 0.049 Uiso 1 1 calc R . .
C27 C 0.0986(5) 0.82583(16) 0.38485(15) 0.0349(7) Uani 1 1 d . . .
H27A H -0.0434 0.8340 0.3718 0.042 Uiso 1 1 calc R . .
C28 C 0.2742(6) 0.92500(19) 0.22667(15) 0.0450(9) Uani 1 1 d . . .
H28A H 0.3833 0.8855 0.2339 0.054 Uiso 1 1 calc R . .
H28B H 0.1702 0.9069 0.1921 0.054 Uiso 1 1 calc R . .
C29 C 0.3649(5) 1.00126(19) 0.20833(14) 0.0370(7) Uani 1 1 d . . .
H29A H 0.3214 1.0121 0.1626 0.044 Uiso 1 1 calc R . .
H29B H 0.5168 0.9981 0.2143 0.044 Uiso 1 1 calc R . .
C30 C 0.2933(5) 1.06653(17) 0.24950(14) 0.0334(7) Uani 1 1 d . . .
H30A H 0.1566 1.0854 0.2311 0.040 Uiso 1 1 calc R . .
H30B H 0.3916 1.1100 0.2510 0.040 Uiso 1 1 calc R . .
C31 C 0.2816(4) 1.03473(15) 0.31705(13) 0.0261(6) Uani 1 1 d . . .
H31A H 0.4238 1.0261 0.3385 0.031 Uiso 1 1 calc R . .
C32 C 0.1622(4) 1.08497(15) 0.35968(13) 0.0253(6) Uani 1 1 d . . .
H32A H 0.0142 1.0822 0.3419 0.030 Uiso 1 1 calc R . .
C33 C 0.2236(4) 1.16959(16) 0.35977(12) 0.0268(6) Uani 1 1 d . . .
C34 C 0.0848(5) 1.22584(17) 0.33809(13) 0.0309(7) Uani 1 1 d . . .
C35 C 0.1341(5) 1.30323(17) 0.33989(15) 0.0373(8) Uani 1 1 d . . .
C36 C 0.3288(6) 1.32572(17) 0.36198(15) 0.0400(8) Uani 1 1 d . . .
C37 C 0.4739(5) 1.27081(17) 0.38348(14) 0.0353(7) Uani 1 1 d . . .
C38 C 0.4190(4) 1.19477(16) 0.38236(13) 0.0302(6) Uani 1 1 d . . .
C39 C 0.0200(5) 1.01689(16) 0.53256(14) 0.0335(7) Uani 1 1 d . . .
C40 C 0.2190(6) 0.9748(2) 0.55122(17) 0.0522(9) Uani 1 1 d . . .
H40A H 0.1944 0.9315 0.5794 0.078 Uiso 1 1 calc R . .
H40B H 0.3190 1.0101 0.5738 0.078 Uiso 1 1 calc R . .
H40C H 0.2730 0.9553 0.5127 0.078 Uiso 1 1 calc R . .
C41 C -0.0612(6) 1.05484(19) 0.59041(16) 0.0448(8) Uani 1 1 d . . .
H41A H -0.0894 1.0152 0.6214 0.067 Uiso 1 1 calc R . .
H41B H -0.1881 1.0829 0.5764 0.067 Uiso 1 1 calc R . .
H41C H 0.0420 1.0908 0.6105 0.067 Uiso 1 1 calc R . .
C42 C -0.1430(6) 0.9661(2) 0.49644(18) 0.0576(11) Uani 1 1 d . . .
H42A H -0.1711 0.9219 0.5232 0.086 Uiso 1 1 calc R . .
H42B H -0.0935 0.9477 0.4568 0.086 Uiso 1 1 calc R . .
H42C H -0.2694 0.9959 0.4860 0.086 Uiso 1 1 calc R . .
S1 S 0.19150(11) 0.50232(4) 0.02554(3) 0.03256(18) Uani 1 1 d . . .
P1 P 0.25186(11) 0.65787(4) 0.20281(3) 0.02521(16) Uani 1 1 d . . .
B1 B -0.0287(6) 0.6263(2) 0.2016(2) 0.0430(9) Uani 1 1 d . . .
H1C H -0.097(5) 0.6825(18) 0.2236(14) 0.038(8) Uiso 1 1 d . . .
H1B H -0.029(4) 0.5776(18) 0.2371(15) 0.039(8) Uiso 1 1 d . . .
H1A H -0.103(6) 0.613(2) 0.1414(18) 0.062(11) Uiso 1 1 d . . .
O1 O 0.3095(4) 0.43514(13) 0.00657(11) 0.0480(6) Uani 1 1 d . . .
N1 N 0.3277(4) 0.55245(13) 0.08419(10) 0.0285(5) Uani 1 1 d . . .
F1 F 0.2396(3) 0.38467(10) 0.21565(9) 0.0496(5) Uani 1 1 d . . .
F2 F 0.4548(5) 0.25369(12) 0.22623(11) 0.0824(8) Uani 1 1 d . . .
F3 F 0.8084(4) 0.23980(13) 0.17068(11) 0.0831(8) Uani 1 1 d . . .
F4 F 0.9399(3) 0.35936(13) 0.10206(10) 0.0628(6) Uani 1 1 d . . .
F5 F 0.7286(3) 0.49006(10) 0.09185(9) 0.0444(5) Uani 1 1 d . . .
C1 C 0.2891(4) 0.73395(15) 0.14648(13) 0.0263(6) Uani 1 1 d . . .
C2 C 0.1181(5) 0.76720(16) 0.11251(14) 0.0323(7) Uani 1 1 d . . .
H2A H -0.0153 0.7493 0.1188 0.039 Uiso 1 1 calc R . .
C3 C 0.1393(5) 0.82628(18) 0.06946(15) 0.0395(8) Uani 1 1 d . . .
H3A H 0.0210 0.8494 0.0470 0.047 Uiso 1 1 calc R . .
C4 C 0.3316(5) 0.85119(19) 0.05938(16) 0.0451(8) Uani 1 1 d . . .
H4A H 0.3469 0.8907 0.0290 0.054 Uiso 1 1 calc R . .
C5 C 0.5019(6) 0.8192(2) 0.0930(2) 0.0531(10) Uani 1 1 d . . .
H5A H 0.6347 0.8372 0.0862 0.064 Uiso 1 1 calc R . .
C6 C 0.4826(5) 0.76048(19) 0.13698(17) 0.0425(8) Uani 1 1 d . . .
H6A H 0.6014 0.7388 0.1603 0.051 Uiso 1 1 calc R . .
C7 C 0.3623(6) 0.68616(19) 0.28302(15) 0.0440(8) Uani 1 1 d . . .
H7A H 0.4273 0.7375 0.2819 0.053 Uiso 1 1 calc R . .
H7B H 0.2541 0.6884 0.3123 0.053 Uiso 1 1 calc R . .
C8 C 0.5223(5) 0.62546(18) 0.30559(15) 0.0363(7) Uani 1 1 d . . .
H8A H 0.6617 0.6450 0.3005 0.044 Uiso 1 1 calc R . .
H8B H 0.5157 0.6140 0.3515 0.044 Uiso 1 1 calc R . .
C9 C 0.4804(5) 0.55259(17) 0.26613(13) 0.0312(7) Uani 1 1 d . . .
H9A H 0.3617 0.5245 0.2801 0.037 Uiso 1 1 calc R . .
H9B H 0.6019 0.5183 0.2711 0.037 Uiso 1 1 calc R . .
C10 C 0.4335(4) 0.57830(14) 0.19586(12) 0.0229(6) Uani 1 1 d . . .
H10A H 0.5620 0.5997 0.1811 0.027 Uiso 1 1 calc R . .
C11 C 0.6568(5) 0.43293(17) 0.12602(14) 0.0340(7) Uani 1 1 d . . .
C12 C 0.7667(5) 0.3659(2) 0.13084(15) 0.0440(8) Uani 1 1 d . . .
C13 C 0.7006(7) 0.3053(2) 0.16518(16) 0.0538(10) Uani 1 1 d . . .
C14 C 0.5227(7) 0.31203(18) 0.19261(16) 0.0519(10) Uani 1 1 d . . .
C15 C 0.4130(5) 0.38101(17) 0.18701(14) 0.0374(7) Uani 1 1 d . . .
C16 C 0.4727(4) 0.44293(17) 0.15376(13) 0.0293(6) Uani 1 1 d . . .
C17 C 0.3469(4) 0.51648(15) 0.14814(13) 0.0256(6) Uani 1 1 d . . .
H17A H 0.2052 0.5035 0.1583 0.031 Uiso 1 1 calc R . .
C18 C 0.2020(5) 0.57510(19) -0.03808(15) 0.0413(8) Uani 1 1 d . . .
C19 C 0.1159(8) 0.5335(3) -0.09856(18) 0.0769(13) Uani 1 1 d . . .
H19A H 0.1157 0.5683 -0.1352 0.115 Uiso 1 1 calc R . .
H19B H -0.0250 0.5167 -0.0944 0.115 Uiso 1 1 calc R . .
H19C H 0.2014 0.4884 -0.1051 0.115 Uiso 1 1 calc R . .
C20 C 0.0692(9) 0.6415(3) -0.0236(2) 0.0850(16) Uani 1 1 d . . .
H20A H 0.0730 0.6810 -0.0568 0.128 Uiso 1 1 calc R . .
H20B H 0.1201 0.6633 0.0182 0.128 Uiso 1 1 calc R . .
H20C H -0.0725 0.6237 -0.0227 0.128 Uiso 1 1 calc R . .
C21 C 0.4249(7) 0.5982(3) -0.0436(2) 0.0776(14) Uani 1 1 d . . .
H21A H 0.4283 0.6370 -0.0773 0.116 Uiso 1 1 calc R . .
H21B H 0.5031 0.5528 -0.0543 0.116 Uiso 1 1 calc R . .
H21C H 0.4861 0.6196 -0.0027 0.116 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O2 1.475(2) . ?
S2 N2 1.692(2) . ?
S2 C39 1.843(3) . ?
P2 C22 1.805(3) . ?
P2 C28 1.824(3) . ?
P2 C31 1.836(3) . ?
P2 B2 1.907(4) . ?
B2 H2C 1.12(4) . ?
B2 H2D 1.09(4) . ?
B2 H2B 0.95(4) . ?
F6 C38 1.349(3) . ?
F7 C37 1.342(4) . ?
F8 C36 1.333(3) . ?
F9 C35 1.349(4) . ?
F10 C34 1.345(3) . ?
N2 C32 1.475(3) . ?
C22 C27 1.377(4) . ?
C22 C23 1.397(4) . ?
C23 C24 1.373(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.397(5) . ?
C24 H24A 0.9500 . ?
C25 C26 1.371(5) . ?
C25 H25A 0.9500 . ?
C26 C27 1.392(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C29 1.518(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.531(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.533(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.527(4) . ?
C31 H31A 1.0000 . ?
C32 C33 1.523(4) . ?
C32 H32A 1.0000 . ?
C33 C34 1.377(4) . ?
C33 C38 1.385(4) . ?
C34 C35 1.382(4) . ?
C35 C36 1.365(5) . ?
C36 C37 1.385(5) . ?
C37 C38 1.368(4) . ?
C39 C40 1.508(5) . ?
C39 C42 1.521(4) . ?
C39 C41 1.529(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
S1 O1 1.478(2) . ?
S1 N1 1.682(2) . ?
S1 C18 1.847(3) . ?
P1 C1 1.809(3) . ?
P1 C7 1.826(3) . ?
P1 C10 1.839(3) . ?
P1 B1 1.914(4) . ?
B1 H1C 1.19(3) . ?
B1 H1B 1.13(3) . ?
B1 H1A 1.32(4) . ?
N1 C17 1.475(3) . ?
F1 C15 1.344(4) . ?
F2 C14 1.339(4) . ?
F3 C13 1.336(4) . ?
F4 C12 1.348(4) . ?
F5 C11 1.340(3) . ?
C1 C6 1.383(4) . ?
C1 C2 1.385(4) . ?
C2 C3 1.385(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.370(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.370(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.524(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.521(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.541(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C17 1.534(4) . ?
C10 H10A 1.0000 . ?
C11 C12 1.367(4) . ?
C11 C16 1.406(4) . ?
C12 C13 1.373(5) . ?
C13 C14 1.361(6) . ?
C14 C15 1.395(5) . ?
C15 C16 1.363(4) . ?
C16 C17 1.517(4) . ?
C17 H17A 1.0000 . ?
C18 C20 1.495(5) . ?
C18 C19 1.516(5) . ?
C18 C21 1.530(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S2 N2 109.12(13) . . ?
O2 S2 C39 106.25(13) . . ?
N2 S2 C39 98.30(12) . . ?
C22 P2 C28 110.40(15) . . ?
C22 P2 C31 111.22(13) . . ?
C28 P2 C31 94.50(14) . . ?
C22 P2 B2 115.05(16) . . ?
C28 P2 B2 112.2(2) . . ?
C31 P2 B2 111.69(16) . . ?
P2 B2 H2C 101.8(19) . . ?
P2 B2 H2D 100(2) . . ?
H2C B2 H2D 111(3) . . ?
P2 B2 H2B 110(2) . . ?
H2C B2 H2B 118(3) . . ?
H2D B2 H2B 114(3) . . ?
C32 N2 S2 115.15(17) . . ?
C27 C22 C23 119.5(3) . . ?
C27 C22 P2 118.2(2) . . ?
C23 C22 P2 122.3(2) . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25A 120.0 . . ?
C24 C25 H25A 120.0 . . ?
C25 C26 C27 120.0(3) . . ?
C25 C26 H26A 120.0 . . ?
C27 C26 H26A 120.0 . . ?
C22 C27 C26 120.3(3) . . ?
C22 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?
C29 C28 P2 107.1(2) . . ?
C29 C28 H28A 110.3 . . ?
P2 C28 H28A 110.3 . . ?
C29 C28 H28B 110.3 . . ?
P2 C28 H28B 110.3 . . ?
H28A C28 H28B 108.6 . . ?
C28 C29 C30 110.5(2) . . ?
C28 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C29 C30 C31 107.9(2) . . ?
C29 C30 H30A 110.1 . . ?
C31 C30 H30A 110.1 . . ?
C29 C30 H30B 110.1 . . ?
C31 C30 H30B 110.1 . . ?
H30A C30 H30B 108.4 . . ?
C32 C31 C30 114.8(2) . . ?
C32 C31 P2 111.74(18) . . ?
C30 C31 P2 101.79(19) . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
P2 C31 H31A 109.4 . . ?
N2 C32 C33 114.2(2) . . ?
N2 C32 C31 107.8(2) . . ?
C33 C32 C31 113.6(2) . . ?
N2 C32 H32A 107.0 . . ?
C33 C32 H32A 107.0 . . ?
C31 C32 H32A 107.0 . . ?
C34 C33 C38 116.1(3) . . ?
C34 C33 C32 121.3(3) . . ?
C38 C33 C32 122.6(2) . . ?
F10 C34 C33 119.8(3) . . ?
F10 C34 C35 117.7(3) . . ?
C33 C34 C35 122.5(3) . . ?
F9 C35 C36 120.3(3) . . ?
F9 C35 C34 120.0(3) . . ?
C36 C35 C34 119.6(3) . . ?
F8 C36 C35 120.5(3) . . ?
F8 C36 C37 119.8(3) . . ?
C35 C36 C37 119.6(3) . . ?
F7 C37 C38 121.0(3) . . ?
F7 C37 C36 119.7(3) . . ?
C38 C37 C36 119.3(3) . . ?
F6 C38 C37 117.9(3) . . ?
F6 C38 C33 119.3(2) . . ?
C37 C38 C33 122.8(3) . . ?
C40 C39 C42 112.7(3) . . ?
C40 C39 C41 111.6(3) . . ?
C42 C39 C41 111.2(3) . . ?
C40 C39 S2 110.3(2) . . ?
C42 C39 S2 106.5(2) . . ?
C41 C39 S2 104.0(2) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O1 S1 N1 110.85(13) . . ?
O1 S1 C18 106.40(14) . . ?
N1 S1 C18 96.74(13) . . ?
C1 P1 C7 109.85(14) . . ?
C1 P1 C10 111.18(12) . . ?
C7 P1 C10 94.71(13) . . ?
C1 P1 B1 113.53(16) . . ?
C7 P1 B1 111.76(18) . . ?
C10 P1 B1 114.29(15) . . ?
P1 B1 H1C 99.2(15) . . ?
P1 B1 H1B 106.1(15) . . ?
H1C B1 H1B 109(2) . . ?
P1 B1 H1A 108.1(16) . . ?
H1C B1 H1A 114(2) . . ?
H1B B1 H1A 118(2) . . ?
C17 N1 S1 115.68(18) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 P1 122.0(2) . . ?
C2 C1 P1 118.8(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
C8 C7 P1 106.8(2) . . ?
C8 C7 H7A 110.4 . . ?
P1 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
P1 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C9 C8 C7 109.2(2) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 106.6(2) . . ?
C8 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
C8 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C17 C10 C9 116.4(2) . . ?
C17 C10 P1 112.48(18) . . ?
C9 C10 P1 101.74(17) . . ?
C17 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
P1 C10 H10A 108.6 . . ?
F5 C11 C12 117.2(3) . . ?
F5 C11 C16 119.9(3) . . ?
C12 C11 C16 122.9(3) . . ?
F4 C12 C11 120.0(3) . . ?
F4 C12 C13 120.1(3) . . ?
C11 C12 C13 119.9(3) . . ?
F3 C13 C14 120.4(4) . . ?
F3 C13 C12 120.2(4) . . ?
C14 C13 C12 119.4(3) . . ?
F2 C14 C13 120.5(3) . . ?
F2 C14 C15 119.8(3) . . ?
C13 C14 C15 119.7(3) . . ?
F1 C15 C16 119.8(3) . . ?
F1 C15 C14 117.1(3) . . ?
C16 C15 C14 123.1(3) . . ?
C15 C16 C11 115.0(3) . . ?
C15 C16 C17 121.3(3) . . ?
C11 C16 C17 123.7(3) . . ?
N1 C17 C16 114.7(2) . . ?
N1 C17 C10 106.7(2) . . ?
C16 C17 C10 112.3(2) . . ?
N1 C17 H17A 107.6 . . ?
C16 C17 H17A 107.6 . . ?
C10 C17 H17A 107.6 . . ?
C20 C18 C19 111.6(3) . . ?
C20 C18 C21 113.2(4) . . ?
C19 C18 C21 109.3(3) . . ?
C20 C18 S1 108.1(3) . . ?
C19 C18 S1 103.9(2) . . ?
C21 C18 S1 110.3(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S2 N2 C32 -94.1(2) . . . . ?
C39 S2 N2 C32 155.4(2) . . . . ?
C28 P2 C22 C27 -122.7(2) . . . . ?
C31 P2 C22 C27 133.7(2) . . . . ?
B2 P2 C22 C27 5.5(3) . . . . ?
C28 P2 C22 C23 55.3(3) . . . . ?
C31 P2 C22 C23 -48.3(3) . . . . ?
B2 P2 C22 C23 -176.5(3) . . . . ?
C27 C22 C23 C24 0.7(4) . . . . ?
P2 C22 C23 C24 -177.2(2) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 C26 -1.2(5) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C23 C22 C27 C26 -0.5(4) . . . . ?
P2 C22 C27 C26 177.6(2) . . . . ?
C25 C26 C27 C22 -0.6(5) . . . . ?
C22 P2 C28 C29 -129.0(2) . . . . ?
C31 P2 C28 C29 -14.4(3) . . . . ?
B2 P2 C28 C29 101.2(3) . . . . ?
P2 C28 C29 C30 -10.0(3) . . . . ?
C28 C29 C30 C31 36.4(4) . . . . ?
C29 C30 C31 C32 -165.1(2) . . . . ?
C29 C30 C31 P2 -44.3(3) . . . . ?
C22 P2 C31 C32 -89.4(2) . . . . ?
C28 P2 C31 C32 156.7(2) . . . . ?
B2 P2 C31 C32 40.7(3) . . . . ?
C22 P2 C31 C30 147.66(18) . . . . ?
C28 P2 C31 C30 33.7(2) . . . . ?
B2 P2 C31 C30 -82.3(2) . . . . ?
S2 N2 C32 C33 51.1(3) . . . . ?
S2 N2 C32 C31 178.25(18) . . . . ?
C30 C31 C32 N2 -175.8(2) . . . . ?
P2 C31 C32 N2 69.0(2) . . . . ?
C30 C31 C32 C33 -48.3(3) . . . . ?
P2 C31 C32 C33 -163.49(19) . . . . ?
N2 C32 C33 C34 -118.0(3) . . . . ?
C31 C32 C33 C34 117.8(3) . . . . ?
N2 C32 C33 C38 60.9(3) . . . . ?
C31 C32 C33 C38 -63.3(3) . . . . ?
C38 C33 C34 F10 179.2(2) . . . . ?
C32 C33 C34 F10 -1.8(4) . . . . ?
C38 C33 C34 C35 -1.5(4) . . . . ?
C32 C33 C34 C35 177.5(3) . . . . ?
F10 C34 C35 F9 -0.2(4) . . . . ?
C33 C34 C35 F9 -179.5(3) . . . . ?
F10 C34 C35 C36 -178.6(3) . . . . ?
C33 C34 C35 C36 2.1(5) . . . . ?
F9 C35 C36 F8 -0.2(5) . . . . ?
C34 C35 C36 F8 178.2(3) . . . . ?
F9 C35 C36 C37 -179.6(3) . . . . ?
C34 C35 C36 C37 -1.2(5) . . . . ?
F8 C36 C37 F7 0.1(4) . . . . ?
C35 C36 C37 F7 179.5(3) . . . . ?
F8 C36 C37 C38 -179.6(3) . . . . ?
C35 C36 C37 C38 -0.2(4) . . . . ?
F7 C37 C38 F6 0.7(4) . . . . ?
C36 C37 C38 F6 -179.6(3) . . . . ?
F7 C37 C38 C33 -178.9(2) . . . . ?
C36 C37 C38 C33 0.8(4) . . . . ?
C34 C33 C38 F6 -179.6(2) . . . . ?
C32 C33 C38 F6 1.4(4) . . . . ?
C34 C33 C38 C37 0.0(4) . . . . ?
C32 C33 C38 C37 -178.9(3) . . . . ?
O2 S2 C39 C40 -59.8(2) . . . . ?
N2 S2 C39 C40 52.9(2) . . . . ?
O2 S2 C39 C42 177.5(2) . . . . ?
N2 S2 C39 C42 -69.7(2) . . . . ?
O2 S2 C39 C41 60.0(2) . . . . ?
N2 S2 C39 C41 172.8(2) . . . . ?
O1 S1 N1 C17 -73.7(2) . . . . ?
C18 S1 N1 C17 175.9(2) . . . . ?
C7 P1 C1 C6 58.9(3) . . . . ?
C10 P1 C1 C6 -44.6(3) . . . . ?
B1 P1 C1 C6 -175.1(3) . . . . ?
C7 P1 C1 C2 -120.2(2) . . . . ?
C10 P1 C1 C2 136.3(2) . . . . ?
B1 P1 C1 C2 5.7(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
P1 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
P1 C1 C6 C5 180.0(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C1 P1 C7 C8 -121.7(2) . . . . ?
C10 P1 C7 C8 -7.1(3) . . . . ?
B1 P1 C7 C8 111.4(3) . . . . ?
P1 C7 C8 C9 -19.6(3) . . . . ?
C7 C8 C9 C10 44.1(3) . . . . ?
C8 C9 C10 C17 -169.0(2) . . . . ?
C8 C9 C10 P1 -46.4(2) . . . . ?
C1 P1 C10 C17 -90.8(2) . . . . ?
C7 P1 C10 C17 155.8(2) . . . . ?
B1 P1 C10 C17 39.4(2) . . . . ?
C1 P1 C10 C9 144.00(18) . . . . ?
C7 P1 C10 C9 30.6(2) . . . . ?
B1 P1 C10 C9 -85.9(2) . . . . ?
F5 C11 C12 F4 0.2(4) . . . . ?
C16 C11 C12 F4 178.7(3) . . . . ?
F5 C11 C12 C13 -179.9(3) . . . . ?
C16 C11 C12 C13 -1.5(5) . . . . ?
F4 C12 C13 F3 0.6(5) . . . . ?
C11 C12 C13 F3 -179.3(3) . . . . ?
F4 C12 C13 C14 -178.4(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
F3 C13 C14 F2 1.0(6) . . . . ?
C12 C13 C14 F2 179.9(3) . . . . ?
F3 C13 C14 C15 179.3(3) . . . . ?
C12 C13 C14 C15 -1.8(6) . . . . ?
F2 C14 C15 F1 -0.9(5) . . . . ?
C13 C14 C15 F1 -179.3(3) . . . . ?
F2 C14 C15 C16 179.8(3) . . . . ?
C13 C14 C15 C16 1.5(5) . . . . ?
F1 C15 C16 C11 179.7(3) . . . . ?
C14 C15 C16 C11 -1.1(5) . . . . ?
F1 C15 C16 C17 -0.1(4) . . . . ?
C14 C15 C16 C17 179.1(3) . . . . ?
F5 C11 C16 C15 179.5(3) . . . . ?
C12 C11 C16 C15 1.1(4) . . . . ?
F5 C11 C16 C17 -0.7(4) . . . . ?
C12 C11 C16 C17 -179.1(3) . . . . ?
S1 N1 C17 C16 67.0(3) . . . . ?
S1 N1 C17 C10 -167.97(17) . . . . ?
C15 C16 C17 N1 -138.8(3) . . . . ?
C11 C16 C17 N1 41.4(4) . . . . ?
C15 C16 C17 C10 99.1(3) . . . . ?
C11 C16 C17 C10 -80.7(3) . . . . ?
C9 C10 C17 N1 -176.2(2) . . . . ?
P1 C10 C17 N1 67.0(2) . . . . ?
C9 C10 C17 C16 -49.7(3) . . . . ?
P1 C10 C17 C16 -166.50(18) . . . . ?
O1 S1 C18 C20 175.2(3) . . . . ?
N1 S1 C18 C20 -70.7(3) . . . . ?
O1 S1 C18 C19 56.5(3) . . . . ?
N1 S1 C18 C19 170.6(3) . . . . ?
O1 S1 C18 C21 -60.5(3) . . . . ?
N1 S1 C18 C21 53.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_403
_database_code_depnum_ccdc_archive 'CCDC 1860469'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2018-11-23 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O2 S'
_chemical_formula_sum            'C19 H20 N2 O2 S'
_chemical_formula_weight         340.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2656(3)
_cell_length_b                   9.5413(3)
_cell_length_c                   13.0878(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.119(3)
_cell_angle_gamma                90
_cell_volume                     893.18(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6593
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4450
_cell_measurement_theta_min      5.7440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1465
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         5.770
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  88.00   1.00    1.00    --    0.00  57.00  60.00   62
  2  ω     56.00  85.00   1.00    1.00    --    0.00  57.00-120.00   29
  3  ω     35.00  88.00   1.00    1.00    --    0.00  38.00 -60.00   53
  4  ω    -17.00   9.00   1.00    1.00    --    0.00  38.00-150.00   26
  5  ω    -14.00  38.00   1.00    1.00    --    0.00  38.00 120.00   52
  6  ω    -21.00  15.00   1.00    1.00    --    0.00  57.00-120.00   36
  7  ω     47.00  73.00   1.00    1.00    --    0.00  38.00 120.00   26
  8  ω     38.00  87.00   1.00    1.00    --    0.00  38.00   0.00   49
  9  ω     29.00  77.00   1.00    1.00    --    0.00  38.00 150.00   48
 10  ω     21.00  52.00   1.00    1.00    --    0.00  38.00-150.00   31
 11  ω    -22.00  21.00   1.00    1.00    --    0.00  57.00  60.00   43
 12  ω     18.00  52.00   1.00    1.00    --    0.00  57.00-120.00   34
 13  ω    -19.00  29.00   1.00    1.00    --    0.00  38.00   0.00   48
 14  ω     -6.00  26.00   1.00    1.00    --    0.00  38.00 -60.00   32
 15  ω     39.00 115.00   1.00    3.00    --   95.80 -82.00  60.00   76
 16  ω     99.00 124.00   1.00    3.00    --   95.80 -82.00-120.00   25
 17  ω    160.00 185.00   1.00    3.00    --   95.80  66.00 -83.48   25
 18  ω     28.00  75.00   1.00    3.00    --   95.80 -82.00-120.00   47
 19  ω     63.00  94.00   1.00    3.00    --   95.80  82.00  30.00   31
 20  ω     69.00 116.00   1.00    3.00    --   95.80  66.00 -83.48   47
 21  ω    156.00 181.00   1.00    3.00    --   95.80  49.00 100.19   25
 22  ω     63.00  89.00   1.00    3.00    --   95.80  82.00 120.00   26
 23  ω     65.00  91.00   1.00    3.00    --   95.80  77.00  90.00   26
 24  ω     75.00 185.00   1.00    3.00    --   95.80  45.00   0.00  110
 25  ω     75.00 168.00   1.00    3.00    --   95.80  45.00  60.00   93
 26  ω     63.00  89.00   1.00    3.00    --   95.80  82.00-150.00   26
 27  ω    125.00 183.00   1.00    3.00    --   95.80  82.00-150.00   58
 28  ω     75.00 184.00   1.00    3.00    --   95.80  45.00-180.00  109
 29  ω      6.00 125.00   1.00    3.00    --   95.80 -82.00 120.00  119
 30  ω     64.00  97.00   1.00    3.00    --   95.80  82.00 -60.00   33
 31  ω    148.00 185.00   1.00    3.00    --   95.80  82.00  60.00   37
 32  ω     66.00  92.00   1.00    3.00    --   95.80  82.00  60.00   26
 33  ω     71.00 157.00   1.00    3.00    --   95.80  64.00-169.85   86
 34  ω    141.00 167.00   1.00    3.00    --   95.80  45.00 -84.72   26
 35  ω      6.00  35.00   1.00    3.00    --   95.80 -61.00 -60.00   29
 36  ω     76.00 127.00   1.00    3.00    --   95.80  45.00 120.00   51
 37  ω      6.00 128.00   1.00    3.00    --   95.80 -82.00 -30.00  122
 38  ω    155.00 181.00   1.00    3.00    --   95.80  45.00  30.00   26
 39  ω     61.00 102.00   1.00    3.00    --   95.80 -61.00 -60.00   41
 40  ω     65.00  91.00   1.00    3.00    --   95.80  82.00 -90.00   26
 41  ω     75.00 150.00   1.00    3.00    --   95.80  45.00  30.00   75
 42  ω     64.00  89.00   1.00    3.00    --   95.80  82.00   0.00   25
 43  ω     71.00  97.00   1.00    3.00    --   95.80  61.00-180.00   26
 44  ω     15.00 103.00   1.00    3.00    --   95.80 -61.00 120.00   88
 45  ω     65.00  90.00   1.00    3.00    --   95.80  77.00-120.00   25
 46  ω     65.00  91.00   1.00    3.00    --   95.80  77.00 150.00   26
 47  ω    135.00 160.00   1.00    3.00    --   95.80  77.00 150.00   25
 48  ω    131.00 156.00   1.00    3.00    --   95.80  56.00 146.78   25
 49  ω     63.00  88.00   1.00    3.00    --   95.80  82.00-180.00   25
 50  ω     75.00 101.00   1.00    3.00    --   95.80  45.00-120.00   26
 51  ω     76.00 101.00   1.00    3.00    --   95.80  45.00 150.00   25
 52  ω     76.00 102.00   1.00    3.00    --   95.80  61.00 -90.00   26
 53  ω     71.00  97.00   1.00    3.00    --   95.80  61.00 120.00   26
 54  ω     65.00  91.00   1.00    3.00    --   95.80  77.00 -30.00   26
 55  ω     70.00 114.00   1.00    3.00    --   95.80 -82.00-150.00   44
 56  ω     76.00 174.00   1.00    3.00    --   95.80  45.00 -30.00   98
 57  ω     65.00  90.00   1.00    3.00    --   95.80  77.00  60.00   25
 58  ω     65.00  91.00   1.00    3.00    --   95.80  82.00 -30.00   26
 59  ω     72.00  99.00   1.00    3.00    --   95.80  56.00 146.78   27
 60  ω     76.00 139.00   1.00    3.00    --   95.80  45.00 -84.72   63
 61  ω     75.00 136.00   1.00    3.00    --   95.80  49.00 100.19   61
 62  ω     73.00 125.00   1.00    3.00    --   95.80  54.00-117.69   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1373824000
_diffrn_orient_matrix_UB_12      -0.0632472000
_diffrn_orient_matrix_UB_13      0.0647050000
_diffrn_orient_matrix_UB_21      0.1316237000
_diffrn_orient_matrix_UB_22      0.0431979000
_diffrn_orient_matrix_UB_23      0.1005113000
_diffrn_orient_matrix_UB_31      -0.1009925000
_diffrn_orient_matrix_UB_32      0.1421496000
_diffrn_orient_matrix_UB_33      -0.0017750000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2544
_reflns_number_total             3162
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1376P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C1(H1A,H1B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C17(H17), C13(H13), C10(H10), C16(H16), C15(H15),
 C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5402(3) 0.5964(2) 0.98685(15) 0.0887(7) Uani 1 1 d . . . . .
N2 N 0.4061(6) 0.4193(5) 0.4588(3) 0.0516(11) Uani 1 1 d . . . . .
H2 H 0.402832 0.334905 0.481559 0.062 Uiso 1 1 calc R . . . .
O2 O 0.5524(6) 0.6284(4) 0.4894(3) 0.0666(12) Uani 1 1 d . . . . .
N1 N 0.7719(8) 0.5371(5) 0.8651(3) 0.0589(12) Uani 1 1 d . . . . .
C7 C 0.5309(7) 0.5069(6) 0.5141(4) 0.0495(12) Uani 1 1 d . . . . .
O1 O 0.5860(11) 0.3563(7) 0.8962(6) 0.114(2) Uani 1 1 d . . . . .
C8 C 0.2791(7) 0.4529(6) 0.3666(4) 0.0514(12) Uani 1 1 d . . . . .
C5 C 0.7499(8) 0.5170(6) 0.6791(4) 0.0520(12) Uani 1 1 d . . . . .
H5 H 0.773129 0.609001 0.661501 0.062 Uiso 1 1 calc R . . . .
C6 C 0.6341(7) 0.4439(6) 0.6116(4) 0.0518(12) Uani 1 1 d . . . . .
H6 H 0.615700 0.349735 0.624973 0.062 Uiso 1 1 calc R . . . .
C9 C 0.0943(8) 0.3974(6) 0.3557(4) 0.0553(13) Uani 1 1 d . . . . .
C4 C 0.8487(8) 0.4643(6) 0.7830(4) 0.0572(13) Uani 1 1 d . . . . .
H4 H 0.820099 0.364380 0.787436 0.069 Uiso 1 1 calc R . . . .
C14 C -0.0323(9) 0.4273(8) 0.2611(5) 0.0671(16) Uani 1 1 d . . . . .
C17 C 0.3316(9) 0.5335(6) 0.2901(5) 0.0603(14) Uani 1 1 d . . . . .
H17 H 0.451956 0.570119 0.299049 0.072 Uiso 1 1 calc R . . . .
C13 C -0.2148(10) 0.3690(9) 0.2497(7) 0.086(2) Uani 1 1 d . . . . .
H13 H -0.299842 0.387917 0.189501 0.104 Uiso 1 1 calc R . . . .
C18 C 1.0603(10) 0.4797(9) 0.7985(5) 0.0761(19) Uani 1 1 d . . . . .
H18A H 1.091642 0.577367 0.790198 0.091 Uiso 1 1 calc R . . . .
H18B H 1.114045 0.451742 0.868707 0.091 Uiso 1 1 calc R . . . .
C3 C 0.6390(11) 0.4758(7) 0.9082(5) 0.0698(16) Uani 1 1 d . . . . .
C10 C 0.0324(9) 0.3154(7) 0.4312(5) 0.0611(14) Uani 1 1 d . . . . .
H10 H 0.113002 0.296753 0.493143 0.073 Uiso 1 1 calc R . . . .
C16 C 0.2047(11) 0.5614(7) 0.1978(5) 0.0726(18) Uani 1 1 d . . . . .
H16 H 0.241877 0.615538 0.145937 0.087 Uiso 1 1 calc R . . . .
C15 C 0.0280(11) 0.5091(8) 0.1845(6) 0.0747(19) Uani 1 1 d . . . . .
H15 H -0.054484 0.528045 0.123302 0.090 Uiso 1 1 calc R . . . .
C11 C -0.1463(10) 0.2618(9) 0.4155(6) 0.0789(19) Uani 1 1 d . . . . .
H11 H -0.185616 0.208123 0.466927 0.095 Uiso 1 1 calc R . . . .
C12 C -0.2689(10) 0.2878(11) 0.3226(8) 0.093(3) Uani 1 1 d . . . . .
H12 H -0.387992 0.248745 0.311368 0.112 Uiso 1 1 calc R . . . .
C1 C 0.7950(12) 0.6870(8) 0.8818(6) 0.0791(19) Uani 1 1 d . . . . .
H1A H 0.747151 0.736831 0.818018 0.095 Uiso 1 1 calc R . . . .
H1B H 0.926713 0.709238 0.901784 0.095 Uiso 1 1 calc R . . . .
C2 C 0.6926(14) 0.7316(10) 0.9646(7) 0.099(3) Uani 1 1 d . . . . .
H2A H 0.621991 0.816230 0.943571 0.119 Uiso 1 1 calc R . . . .
H2B H 0.780315 0.751488 1.027749 0.119 Uiso 1 1 calc R . . . .
C19 C 1.1437(13) 0.3927(13) 0.7232(7) 0.103(3) Uani 1 1 d . . . . .
H19A H 1.091254 0.420319 0.653677 0.155 Uiso 1 1 calc GR . . . .
H19B H 1.116596 0.295573 0.732863 0.155 Uiso 1 1 calc GR . . . .
H19C H 1.276619 0.406279 0.734846 0.155 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.777(7) . ?
S1 C2 1.758(11) . ?
N2 H2 0.8600 . ?
N2 C7 1.347(7) . ?
N2 C8 1.421(7) . ?
O2 C7 1.221(7) . ?
N1 C4 1.469(8) . ?
N1 C3 1.336(8) . ?
N1 C1 1.452(8) . ?
C7 C6 1.488(7) . ?
O1 C3 1.205(9) . ?
C8 C9 1.427(8) . ?
C8 C17 1.369(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.309(7) . ?
C5 C4 1.509(8) . ?
C6 H6 0.9300 . ?
C9 C14 1.435(8) . ?
C9 C10 1.396(9) . ?
C4 H4 0.9800 . ?
C4 C18 1.522(10) . ?
C14 C13 1.421(11) . ?
C14 C15 1.400(11) . ?
C17 H17 0.9300 . ?
C17 C16 1.411(9) . ?
C13 H13 0.9300 . ?
C13 C12 1.340(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.496(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(10) . ?
C16 H16 0.9300 . ?
C16 C15 1.360(12) . ?
C15 H15 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.397(12) . ?
C12 H12 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.481(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C3 92.8(4) . . ?
C7 N2 H2 116.9 . . ?
C7 N2 C8 126.2(5) . . ?
C8 N2 H2 116.9 . . ?
C3 N1 C4 119.9(5) . . ?
C3 N1 C1 116.1(6) . . ?
C1 N1 C4 121.8(5) . . ?
N2 C7 C6 113.6(5) . . ?
O2 C7 N2 123.6(5) . . ?
O2 C7 C6 122.8(5) . . ?
N2 C8 C9 117.4(5) . . ?
C17 C8 N2 121.7(5) . . ?
C17 C8 C9 120.9(5) . . ?
C6 C5 H5 117.3 . . ?
C6 C5 C4 125.4(5) . . ?
C4 C5 H5 117.3 . . ?
C7 C6 H6 119.0 . . ?
C5 C6 C7 122.1(5) . . ?
C5 C6 H6 119.0 . . ?
C8 C9 C14 117.5(6) . . ?
C10 C9 C8 123.5(5) . . ?
C10 C9 C14 119.0(6) . . ?
N1 C4 C5 108.7(5) . . ?
N1 C4 H4 107.8 . . ?
N1 C4 C18 111.2(5) . . ?
C5 C4 H4 107.8 . . ?
C5 C4 C18 113.4(5) . . ?
C18 C4 H4 107.8 . . ?
C13 C14 C9 117.2(7) . . ?
C15 C14 C9 119.6(6) . . ?
C15 C14 C13 123.2(6) . . ?
C8 C17 H17 119.7 . . ?
C8 C17 C16 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
C14 C13 H13 118.8 . . ?
C12 C13 C14 122.5(7) . . ?
C12 C13 H13 118.8 . . ?
C4 C18 H18A 109.2 . . ?
C4 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C4 112.0(7) . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N1 C3 S1 110.9(5) . . ?
O1 C3 S1 122.4(6) . . ?
O1 C3 N1 126.6(6) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10 119.5 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(7) . . ?
C15 C16 H16 120.0 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(6) . . ?
C16 C15 H15 119.3 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(7) . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.0(7) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.5(7) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
S1 C2 H2A 109.9 . . ?
S1 C2 H2B 109.9 . . ?
C1 C2 S1 108.8(6) . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.276
_oxdiff_exptl_absorpt_empirical_full_min 0.136
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1819864'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang'
;East China Normal University
China
;
_audit_update_record             
;
2018-08-04 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 B F5 N O P S'
_chemical_formula_weight         477.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   17.1138(14)
_cell_length_b                   6.6266(5)
_cell_length_c                   20.6037(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.452(3)
_cell_angle_gamma                90.00
_cell_volume                     2332.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9284
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27239
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7869
_reflns_number_gt                6051
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+5.0384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7869
_refine_ls_number_parameters     583
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P2 P 0.97372(9) 0.6701(3) 0.15570(8) 0.0314(4) Uani 1 1 d . . .
S2 S 0.84928(11) 0.8379(3) 0.38443(8) 0.0488(5) Uani 1 1 d . . .
O2 O 0.7650(3) 0.8145(15) 0.3887(3) 0.101(3) Uani 1 1 d . . .
N2 N 0.8713(3) 0.9285(9) 0.3118(2) 0.0371(13) Uani 1 1 d . . .
H2B H 0.8751 1.0588 0.3044 0.044 Uiso 1 1 calc R . .
F6 F 0.8060(2) 0.4034(7) 0.2774(2) 0.0565(12) Uani 1 1 d . . .
F7 F 0.6735(2) 0.2881(7) 0.2126(2) 0.0606(13) Uani 1 1 d . . .
F8 F 0.6005(2) 0.5444(8) 0.1262(2) 0.0564(12) Uani 1 1 d . . .
F9 F 0.6626(2) 0.9094(8) 0.1037(2) 0.0614(12) Uani 1 1 d . . .
F10 F 0.7954(2) 1.0285(6) 0.16819(19) 0.0459(10) Uani 1 1 d . . .
B2 B 0.9643(7) 0.3922(14) 0.1786(5) 0.055(2) Uani 1 1 d . . .
H2E H 0.995(5) 0.329(13) 0.138(4) 0.07(2) Uiso 1 1 d . . .
H2D H 0.912(4) 0.343(11) 0.180(3) 0.05(2) Uiso 1 1 d . . .
H2C H 0.993(3) 0.387(9) 0.229(3) 0.023(15) Uiso 1 1 d . . .
C22 C 0.9236(4) 0.7404(11) 0.0799(3) 0.0392(17) Uani 1 1 d . . .
C23 C 0.8864(4) 0.5935(12) 0.0409(4) 0.0476(19) Uani 1 1 d . . .
H23A H 0.8859 0.4574 0.0554 0.057 Uiso 1 1 calc R . .
C24 C 0.8499(4) 0.6449(16) -0.0194(4) 0.058(2) Uani 1 1 d . . .
H24A H 0.8237 0.5440 -0.0453 0.069 Uiso 1 1 calc R . .
C25 C 0.8515(5) 0.8388(16) -0.0412(4) 0.064(2) Uani 1 1 d . . .
H25A H 0.8282 0.8730 -0.0827 0.077 Uiso 1 1 calc R . .
C26 C 0.8876(6) 0.9855(15) -0.0021(4) 0.074(3) Uani 1 1 d . . .
H26A H 0.8866 1.1222 -0.0160 0.089 Uiso 1 1 calc R . .
C27 C 0.9250(5) 0.9347(13) 0.0571(4) 0.055(2) Uani 1 1 d . . .
H27A H 0.9521 1.0358 0.0822 0.066 Uiso 1 1 calc R . .
C28 C 1.0754(4) 0.7492(12) 0.1548(4) 0.0432(17) Uani 1 1 d . . .
H28A H 1.1106 0.6333 0.1648 0.052 Uiso 1 1 calc R . .
H28B H 1.0864 0.8024 0.1114 0.052 Uiso 1 1 calc R . .
C29 C 1.0885(4) 0.9129(12) 0.2061(3) 0.0414(16) Uani 1 1 d . . .
H29A H 1.0827 1.0478 0.1858 0.050 Uiso 1 1 calc R . .
H29B H 1.1419 0.9020 0.2270 0.050 Uiso 1 1 calc R . .
C30 C 1.0274(4) 0.8846(11) 0.2569(3) 0.0374(15) Uani 1 1 d . . .
H30A H 1.0254 1.0055 0.2849 0.045 Uiso 1 1 calc R . .
H30B H 1.0408 0.7661 0.2846 0.045 Uiso 1 1 calc R . .
C31 C 0.9478(4) 0.8521(10) 0.2188(3) 0.0307(14) Uani 1 1 d . . .
H31A H 0.9308 0.9817 0.1975 0.037 Uiso 1 1 calc R . .
C32 C 0.8074(4) 0.7176(10) 0.2246(3) 0.0325(15) Uani 1 1 d . . .
C33 C 0.7739(4) 0.5328(11) 0.2344(3) 0.0390(17) Uani 1 1 d . . .
C34 C 0.7048(4) 0.4735(11) 0.2020(4) 0.0424(17) Uani 1 1 d . . .
C35 C 0.6676(4) 0.5971(12) 0.1569(3) 0.0407(18) Uani 1 1 d . . .
C36 C 0.6994(4) 0.7851(12) 0.1461(3) 0.0398(17) Uani 1 1 d . . .
C37 C 0.7678(4) 0.8432(10) 0.1799(3) 0.0329(15) Uani 1 1 d . . .
C38 C 0.8838(4) 0.7790(10) 0.2620(3) 0.0323(15) Uani 1 1 d . . .
H38A H 0.9045 0.6554 0.2850 0.039 Uiso 1 1 calc R . .
C39 C 0.8794(6) 1.0508(16) 0.4361(4) 0.071(2) Uani 1 1 d U . .
C40 C 0.9601(7) 1.097(2) 0.4266(6) 0.116(4) Uani 1 1 d U . .
H40A H 0.9769 1.2107 0.4544 0.175 Uiso 1 1 calc R . .
H40B H 0.9658 1.1321 0.3809 0.175 Uiso 1 1 calc R . .
H40C H 0.9926 0.9786 0.4380 0.175 Uiso 1 1 calc R . .
C41 C 0.8241(12) 1.223(2) 0.4220(5) 0.190(9) Uani 1 1 d U . .
H41A H 0.8403 1.3394 0.4490 0.285 Uiso 1 1 calc R . .
H41B H 0.7710 1.1829 0.4317 0.285 Uiso 1 1 calc R . .
H41C H 0.8249 1.2605 0.3760 0.285 Uiso 1 1 calc R . .
C42 C 0.8671(5) 0.9781(19) 0.5044(4) 0.083(3) Uani 1 1 d U . .
H42A H 0.8832 1.0839 0.5356 0.124 Uiso 1 1 calc R . .
H42B H 0.8986 0.8566 0.5134 0.124 Uiso 1 1 calc R . .
H42C H 0.8117 0.9466 0.5082 0.124 Uiso 1 1 calc R . .
S1 S 0.67762(9) 0.4083(3) -0.11908(7) 0.0348(4) Uani 1 1 d . . .
P1 P 0.50750(9) 0.6675(3) -0.33681(8) 0.0296(4) Uani 1 1 d . . .
F1 F 0.6797(2) 0.2654(6) -0.32436(18) 0.0463(10) Uani 1 1 d . . .
F2 F 0.8026(3) 0.3697(9) -0.3900(2) 0.0750(16) Uani 1 1 d . . .
F3 F 0.8735(2) 0.7315(9) -0.3673(2) 0.0788(18) Uani 1 1 d . . .
F4 F 0.8186(3) 0.9894(8) -0.2787(3) 0.0751(16) Uani 1 1 d . . .
F5 F 0.6957(2) 0.8834(6) -0.21211(19) 0.0494(10) Uani 1 1 d . . .
O1 O 0.7534(3) 0.3068(9) -0.1243(2) 0.0509(14) Uani 1 1 d . . .
N1 N 0.6188(3) 0.3567(8) -0.1844(2) 0.0336(13) Uani 1 1 d . . .
H1A H 0.5963 0.2381 -0.1902 0.040 Uiso 1 1 calc R . .
B1 B 0.5162(6) 0.9383(12) -0.3034(5) 0.047(2) Uani 1 1 d . . .
H1D H 0.477(8) 1.02(3) -0.350(7) 0.19(6) Uiso 1 1 d . . .
H1C H 0.578(5) 0.987(14) -0.292(4) 0.08(3) Uiso 1 1 d . . .
H1B H 0.477(4) 0.925(12) -0.262(4) 0.06(2) Uiso 1 1 d . . .
C1 C 0.5587(4) 0.6263(11) -0.4089(3) 0.0375(17) Uani 1 1 d U . .
C2 C 0.5570(4) 0.4399(13) -0.4410(3) 0.052(2) Uani 1 1 d U . .
H2A H 0.5269 0.3323 -0.4250 0.062 Uiso 1 1 calc R . .
C3 C 0.5981(5) 0.4110(18) -0.4950(4) 0.071(3) Uani 1 1 d U . .
H3A H 0.5961 0.2841 -0.5165 0.085 Uiso 1 1 calc R . .
C4 C 0.6433(5) 0.569(2) -0.5190(4) 0.076(3) Uani 1 1 d U . .
H4A H 0.6713 0.5497 -0.5569 0.091 Uiso 1 1 calc R . .
C5 C 0.6465(5) 0.7473(17) -0.4877(4) 0.066(3) Uani 1 1 d U . .
H5A H 0.6777 0.8536 -0.5031 0.079 Uiso 1 1 calc R . .
C6 C 0.6045(4) 0.7763(12) -0.4331(3) 0.0435(18) Uani 1 1 d U . .
H6A H 0.6074 0.9033 -0.4117 0.052 Uiso 1 1 calc R . .
C7 C 0.5360(3) 0.4702(9) -0.2777(3) 0.0274(14) Uani 1 1 d . . .
H7A H 0.5483 0.3450 -0.3022 0.033 Uiso 1 1 calc R . .
C8 C 0.4596(3) 0.4342(11) -0.2432(3) 0.0342(15) Uani 1 1 d . . .
H8A H 0.4493 0.5478 -0.2137 0.041 Uiso 1 1 calc R . .
H8B H 0.4631 0.3080 -0.2175 0.041 Uiso 1 1 calc R . .
C9 C 0.3939(4) 0.4184(11) -0.2978(3) 0.0373(15) Uani 1 1 d . . .
H9A H 0.3948 0.2831 -0.3182 0.045 Uiso 1 1 calc R . .
H9B H 0.3423 0.4374 -0.2795 0.045 Uiso 1 1 calc R . .
C10 C 0.4064(4) 0.5796(11) -0.3486(3) 0.0395(16) Uani 1 1 d . . .
H10A H 0.3698 0.6932 -0.3434 0.047 Uiso 1 1 calc R . .
H10B H 0.3969 0.5229 -0.3928 0.047 Uiso 1 1 calc R . .
C11 C 0.6806(3) 0.5723(10) -0.2676(3) 0.0283(14) Uani 1 1 d . . .
C12 C 0.7112(4) 0.4459(11) -0.3126(3) 0.0376(16) Uani 1 1 d . . .
C13 C 0.7756(4) 0.5022(14) -0.3473(3) 0.049(2) Uani 1 1 d . . .
C14 C 0.8095(4) 0.6837(16) -0.3355(4) 0.051(2) Uani 1 1 d . . .
C15 C 0.7827(4) 0.8093(12) -0.2908(4) 0.0451(18) Uani 1 1 d . . .
C16 C 0.7186(4) 0.7519(11) -0.2572(3) 0.0346(15) Uani 1 1 d . . .
C17 C 0.6068(3) 0.5210(10) -0.2316(3) 0.0296(14) Uani 1 1 d . . .
H17A H 0.5929 0.6441 -0.2068 0.036 Uiso 1 1 calc R . .
C18 C 0.6253(4) 0.2683(12) -0.0572(3) 0.0412(17) Uani 1 1 d . . .
C19 C 0.5474(5) 0.3724(14) -0.0520(4) 0.062(2) Uani 1 1 d . . .
H19B H 0.5175 0.3031 -0.0196 0.093 Uiso 1 1 calc R . .
H19C H 0.5180 0.3688 -0.0943 0.093 Uiso 1 1 calc R . .
H19D H 0.5561 0.5130 -0.0388 0.093 Uiso 1 1 calc R . .
C20 C 0.6782(5) 0.2931(14) 0.0042(3) 0.058(2) Uani 1 1 d . . .
H20B H 0.6550 0.2235 0.0403 0.088 Uiso 1 1 calc R . .
H20C H 0.6840 0.4369 0.0145 0.088 Uiso 1 1 calc R . .
H20D H 0.7297 0.2349 -0.0027 0.088 Uiso 1 1 calc R . .
C21 C 0.6169(5) 0.0496(12) -0.0771(4) 0.058(2) Uani 1 1 d . . .
H21B H 0.5889 -0.0240 -0.0444 0.087 Uiso 1 1 calc R . .
H21C H 0.6689 -0.0098 -0.0806 0.087 Uiso 1 1 calc R . .
H21D H 0.5874 0.0407 -0.1193 0.087 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P2 C22 1.797(7) . ?
P2 C28 1.818(7) . ?
P2 C31 1.847(6) . ?
P2 B2 1.910(10) . ?
S2 O2 1.459(6) . ?
S2 N2 1.676(5) . ?
S2 C39 1.823(9) . ?
N2 C38 1.451(8) . ?
N2 H2B 0.8800 . ?
F6 C33 1.328(8) . ?
F7 C34 1.363(8) . ?
F8 C35 1.324(8) . ?
F9 C36 1.331(8) . ?
F10 C37 1.343(8) . ?
B2 H2E 1.09(8) . ?
B2 H2D 0.95(7) . ?
B2 H2C 1.13(5) . ?
C22 C27 1.371(11) . ?
C22 C23 1.391(10) . ?
C23 C24 1.400(10) . ?
C23 H23A 0.9500 . ?
C24 C25 1.362(13) . ?
C24 H24A 0.9500 . ?
C25 C26 1.383(13) . ?
C25 H25A 0.9500 . ?
C26 C27 1.385(11) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C29 1.522(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.533(9) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.546(9) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C38 1.532(8) . ?
C31 H31A 1.0000 . ?
C32 C33 1.373(9) . ?
C32 C37 1.387(8) . ?
C32 C38 1.532(9) . ?
C33 C34 1.379(10) . ?
C34 C35 1.368(10) . ?
C35 C36 1.382(10) . ?
C36 C37 1.381(9) . ?
C38 H38A 1.0000 . ?
C39 C40 1.440(15) . ?
C39 C41 1.502(15) . ?
C39 C42 1.512(11) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
S1 O1 1.471(5) . ?
S1 N1 1.668(5) . ?
S1 C18 1.851(7) . ?
P1 C1 1.791(7) . ?
P1 C10 1.827(6) . ?
P1 C7 1.832(6) . ?
P1 B1 1.924(8) . ?
F1 C12 1.329(8) . ?
F2 C13 1.345(9) . ?
F3 C14 1.347(8) . ?
F4 C15 1.358(9) . ?
F5 C16 1.348(8) . ?
N1 C17 1.466(8) . ?
N1 H1A 0.8800 . ?
B1 H1D 1.26(15) . ?
B1 H1C 1.12(9) . ?
B1 H1B 1.12(7) . ?
C1 C6 1.378(9) . ?
C1 C2 1.401(10) . ?
C2 C3 1.365(10) . ?
C2 H2A 0.9500 . ?
C3 C4 1.408(14) . ?
C3 H3A 0.9500 . ?
C4 C5 1.346(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(11) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C17 1.531(8) . ?
C7 C8 1.545(8) . ?
C7 H7A 1.0000 . ?
C8 C9 1.545(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.367(9) . ?
C11 C12 1.376(9) . ?
C11 C17 1.540(8) . ?
C12 C13 1.399(10) . ?
C13 C14 1.351(12) . ?
C14 C15 1.343(12) . ?
C15 C16 1.386(9) . ?
C17 H17A 1.0000 . ?
C18 C21 1.510(11) . ?
C18 C19 1.511(10) . ?
C18 C20 1.520(10) . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 H20D 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 P2 C28 108.9(3) . . ?
C22 P2 C31 108.7(3) . . ?
C28 P2 C31 95.1(3) . . ?
C22 P2 B2 115.0(4) . . ?
C28 P2 B2 112.0(4) . . ?
C31 P2 B2 115.3(4) . . ?
O2 S2 N2 111.6(3) . . ?
O2 S2 C39 107.0(5) . . ?
N2 S2 C39 100.0(4) . . ?
C38 N2 S2 115.9(5) . . ?
C38 N2 H2B 122.1 . . ?
S2 N2 H2B 122.1 . . ?
P2 B2 H2E 98(5) . . ?
P2 B2 H2D 115(5) . . ?
H2E B2 H2D 112(6) . . ?
P2 B2 H2C 103(3) . . ?
H2E B2 H2C 119(5) . . ?
H2D B2 H2C 109(5) . . ?
C27 C22 C23 118.4(7) . . ?
C27 C22 P2 121.6(6) . . ?
C23 C22 P2 119.9(6) . . ?
C22 C23 C24 120.5(8) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C25 C24 C23 120.3(8) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C24 C25 C26 119.3(8) . . ?
C24 C25 H25A 120.4 . . ?
C26 C25 H25A 120.4 . . ?
C25 C26 C27 120.5(9) . . ?
C25 C26 H26A 119.7 . . ?
C27 C26 H26A 119.7 . . ?
C22 C27 C26 120.9(8) . . ?
C22 C27 H27A 119.5 . . ?
C26 C27 H27A 119.5 . . ?
C29 C28 P2 107.4(4) . . ?
C29 C28 H28A 110.2 . . ?
P2 C28 H28A 110.2 . . ?
C29 C28 H28B 110.2 . . ?
P2 C28 H28B 110.2 . . ?
H28A C28 H28B 108.5 . . ?
C28 C29 C30 108.0(6) . . ?
C28 C29 H29A 110.1 . . ?
C30 C29 H29A 110.1 . . ?
C28 C29 H29B 110.1 . . ?
C30 C29 H29B 110.1 . . ?
H29A C29 H29B 108.4 . . ?
C29 C30 C31 106.7(5) . . ?
C29 C30 H30A 110.4 . . ?
C31 C30 H30A 110.4 . . ?
C29 C30 H30B 110.4 . . ?
C31 C30 H30B 110.4 . . ?
H30A C30 H30B 108.6 . . ?
C38 C31 C30 112.9(5) . . ?
C38 C31 P2 114.4(4) . . ?
C30 C31 P2 101.9(4) . . ?
C38 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
P2 C31 H31A 109.1 . . ?
C33 C32 C37 116.2(6) . . ?
C33 C32 C38 120.9(6) . . ?
C37 C32 C38 122.8(6) . . ?
F6 C33 C32 120.9(6) . . ?
F6 C33 C34 116.6(6) . . ?
C32 C33 C34 122.4(7) . . ?
F7 C34 C35 118.5(6) . . ?
F7 C34 C33 120.9(7) . . ?
C35 C34 C33 120.6(7) . . ?
F8 C35 C34 121.4(7) . . ?
F8 C35 C36 120.0(7) . . ?
C34 C35 C36 118.5(6) . . ?
F9 C36 C37 120.8(7) . . ?
F9 C36 C35 119.2(6) . . ?
C37 C36 C35 120.0(6) . . ?
F10 C37 C36 117.5(6) . . ?
F10 C37 C32 120.3(6) . . ?
C36 C37 C32 122.2(6) . . ?
N2 C38 C31 109.6(5) . . ?
N2 C38 C32 112.4(5) . . ?
C31 C38 C32 114.2(5) . . ?
N2 C38 H38A 106.7 . . ?
C31 C38 H38A 106.7 . . ?
C32 C38 H38A 106.7 . . ?
C40 C39 C41 114.3(12) . . ?
C40 C39 C42 112.5(9) . . ?
C41 C39 C42 107.6(9) . . ?
C40 C39 S2 108.9(8) . . ?
C41 C39 S2 108.8(8) . . ?
C42 C39 S2 104.3(7) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O1 S1 N1 109.8(3) . . ?
O1 S1 C18 106.7(3) . . ?
N1 S1 C18 99.2(3) . . ?
C1 P1 C10 110.3(3) . . ?
C1 P1 C7 108.6(3) . . ?
C10 P1 C7 94.2(3) . . ?
C1 P1 B1 114.1(4) . . ?
C10 P1 B1 113.4(4) . . ?
C7 P1 B1 114.6(4) . . ?
C17 N1 S1 115.9(4) . . ?
C17 N1 H1A 122.0 . . ?
S1 N1 H1A 122.0 . . ?
P1 B1 H1D 95(8) . . ?
P1 B1 H1C 113(5) . . ?
H1D B1 H1C 120(8) . . ?
P1 B1 H1B 99(4) . . ?
H1D B1 H1B 108(7) . . ?
H1C B1 H1B 117(6) . . ?
C6 C1 C2 117.5(7) . . ?
C6 C1 P1 120.5(6) . . ?
C2 C1 P1 121.9(5) . . ?
C3 C2 C1 120.8(8) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C2 C3 C4 120.1(10) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.5(8) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 121.9(8) . . ?
C1 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C17 C7 C8 114.1(5) . . ?
C17 C7 P1 115.1(4) . . ?
C8 C7 P1 102.5(4) . . ?
C17 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
P1 C7 H7A 108.2 . . ?
C7 C8 C9 105.9(5) . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C8 109.1(5) . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 P1 107.8(4) . . ?
C9 C10 H10A 110.2 . . ?
P1 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
P1 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C16 C11 C12 116.1(6) . . ?
C16 C11 C17 120.8(6) . . ?
C12 C11 C17 123.1(6) . . ?
F1 C12 C11 120.2(6) . . ?
F1 C12 C13 118.1(7) . . ?
C11 C12 C13 121.7(7) . . ?
F2 C13 C14 122.5(7) . . ?
F2 C13 C12 118.2(8) . . ?
C14 C13 C12 119.2(7) . . ?
C15 C14 F3 120.6(9) . . ?
C15 C14 C13 121.0(7) . . ?
F3 C14 C13 118.4(9) . . ?
C14 C15 F4 120.1(7) . . ?
C14 C15 C16 119.1(7) . . ?
F4 C15 C16 120.8(8) . . ?
F5 C16 C11 121.1(6) . . ?
F5 C16 C15 116.0(6) . . ?
C11 C16 C15 122.9(7) . . ?
N1 C17 C7 108.8(5) . . ?
N1 C17 C11 113.4(5) . . ?
C7 C17 C11 113.0(5) . . ?
N1 C17 H17A 107.1 . . ?
C7 C17 H17A 107.1 . . ?
C11 C17 H17A 107.1 . . ?
C21 C18 C19 112.8(7) . . ?
C21 C18 C20 111.8(7) . . ?
C19 C18 C20 112.1(6) . . ?
C21 C18 S1 109.6(5) . . ?
C19 C18 S1 106.6(5) . . ?
C20 C18 S1 103.3(5) . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C19 H19D 109.5 . . ?
H19B C19 H19D 109.5 . . ?
H19C C19 H19D 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C20 H20D 109.5 . . ?
H20B C20 H20D 109.5 . . ?
H20C C20 H20D 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C21 H21D 109.5 . . ?
H21B C21 H21D 109.5 . . ?
H21C C21 H21D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S2 N2 C38 -89.8(6) . . . . ?
C39 S2 N2 C38 157.3(5) . . . . ?
C28 P2 C22 C27 -53.4(7) . . . . ?
C31 P2 C22 C27 49.0(7) . . . . ?
B2 P2 C22 C27 180.0(7) . . . . ?
C28 P2 C22 C23 122.4(6) . . . . ?
C31 P2 C22 C23 -135.2(6) . . . . ?
B2 P2 C22 C23 -4.2(8) . . . . ?
C27 C22 C23 C24 -1.5(11) . . . . ?
P2 C22 C23 C24 -177.5(6) . . . . ?
C22 C23 C24 C25 1.2(12) . . . . ?
C23 C24 C25 C26 -2.1(13) . . . . ?
C24 C25 C26 C27 3.2(14) . . . . ?
C23 C22 C27 C26 2.7(12) . . . . ?
P2 C22 C27 C26 178.5(7) . . . . ?
C25 C26 C27 C22 -3.6(14) . . . . ?
C22 P2 C28 C29 113.8(5) . . . . ?
C31 P2 C28 C29 2.1(6) . . . . ?
B2 P2 C28 C29 -117.9(6) . . . . ?
P2 C28 C29 C30 24.5(7) . . . . ?
C28 C29 C30 C31 -46.4(7) . . . . ?
C29 C30 C31 C38 168.3(6) . . . . ?
C29 C30 C31 P2 45.1(6) . . . . ?
C22 P2 C31 C38 98.9(5) . . . . ?
C28 P2 C31 C38 -149.2(5) . . . . ?
B2 P2 C31 C38 -31.8(6) . . . . ?
C22 P2 C31 C30 -138.9(4) . . . . ?
C28 P2 C31 C30 -27.0(5) . . . . ?
B2 P2 C31 C30 90.3(6) . . . . ?
C37 C32 C33 F6 -178.2(6) . . . . ?
C38 C32 C33 F6 1.1(10) . . . . ?
C37 C32 C33 C34 0.0(10) . . . . ?
C38 C32 C33 C34 179.3(6) . . . . ?
F6 C33 C34 F7 -2.2(10) . . . . ?
C32 C33 C34 F7 179.5(6) . . . . ?
F6 C33 C34 C35 -180.0(6) . . . . ?
C32 C33 C34 C35 1.7(11) . . . . ?
F7 C34 C35 F8 3.5(10) . . . . ?
C33 C34 C35 F8 -178.7(6) . . . . ?
F7 C34 C35 C36 -179.9(6) . . . . ?
C33 C34 C35 C36 -2.1(10) . . . . ?
F8 C35 C36 F9 -1.4(9) . . . . ?
C34 C35 C36 F9 -178.0(6) . . . . ?
F8 C35 C36 C37 177.5(6) . . . . ?
C34 C35 C36 C37 0.9(10) . . . . ?
F9 C36 C37 F10 -0.2(9) . . . . ?
C35 C36 C37 F10 -179.0(6) . . . . ?
F9 C36 C37 C32 179.7(6) . . . . ?
C35 C36 C37 C32 0.9(10) . . . . ?
C33 C32 C37 F10 178.6(6) . . . . ?
C38 C32 C37 F10 -0.7(9) . . . . ?
C33 C32 C37 C36 -1.3(9) . . . . ?
C38 C32 C37 C36 179.4(6) . . . . ?
S2 N2 C38 C31 -144.9(4) . . . . ?
S2 N2 C38 C32 87.1(6) . . . . ?
C30 C31 C38 N2 60.9(7) . . . . ?
P2 C31 C38 N2 176.9(4) . . . . ?
C30 C31 C38 C32 -172.0(5) . . . . ?
P2 C31 C38 C32 -56.1(7) . . . . ?
C33 C32 C38 N2 -106.8(7) . . . . ?
C37 C32 C38 N2 72.5(7) . . . . ?
C33 C32 C38 C31 127.6(7) . . . . ?
C37 C32 C38 C31 -53.2(8) . . . . ?
O2 S2 C39 C40 -172.3(8) . . . . ?
N2 S2 C39 C40 -55.8(8) . . . . ?
O2 S2 C39 C41 -47.1(10) . . . . ?
N2 S2 C39 C41 69.3(9) . . . . ?
O2 S2 C39 C42 67.4(7) . . . . ?
N2 S2 C39 C42 -176.1(6) . . . . ?
O1 S1 N1 C17 -105.9(5) . . . . ?
C18 S1 N1 C17 142.6(5) . . . . ?
C10 P1 C1 C6 134.0(5) . . . . ?
C7 P1 C1 C6 -124.1(5) . . . . ?
B1 P1 C1 C6 5.0(7) . . . . ?
C10 P1 C1 C2 -49.2(7) . . . . ?
C7 P1 C1 C2 52.7(6) . . . . ?
B1 P1 C1 C2 -178.1(6) . . . . ?
C6 C1 C2 C3 -1.4(11) . . . . ?
P1 C1 C2 C3 -178.4(6) . . . . ?
C1 C2 C3 C4 0.4(12) . . . . ?
C2 C3 C4 C5 0.9(14) . . . . ?
C3 C4 C5 C6 -1.2(13) . . . . ?
C2 C1 C6 C5 1.2(10) . . . . ?
P1 C1 C6 C5 178.2(6) . . . . ?
C4 C5 C6 C1 0.1(12) . . . . ?
C1 P1 C7 C17 90.3(5) . . . . ?
C10 P1 C7 C17 -156.6(5) . . . . ?
B1 P1 C7 C17 -38.5(6) . . . . ?
C1 P1 C7 C8 -145.2(4) . . . . ?
C10 P1 C7 C8 -32.1(5) . . . . ?
B1 P1 C7 C8 86.0(5) . . . . ?
C17 C7 C8 C9 171.5(5) . . . . ?
P1 C7 C8 C9 46.4(6) . . . . ?
C7 C8 C9 C10 -42.2(7) . . . . ?
C8 C9 C10 P1 17.4(7) . . . . ?
C1 P1 C10 C9 120.6(5) . . . . ?
C7 P1 C10 C9 9.0(5) . . . . ?
B1 P1 C10 C9 -110.1(6) . . . . ?
C16 C11 C12 F1 177.7(5) . . . . ?
C17 C11 C12 F1 -3.7(9) . . . . ?
C16 C11 C12 C13 -2.4(9) . . . . ?
C17 C11 C12 C13 176.2(6) . . . . ?
F1 C12 C13 F2 -0.7(9) . . . . ?
C11 C12 C13 F2 179.4(6) . . . . ?
F1 C12 C13 C14 -179.0(6) . . . . ?
C11 C12 C13 C14 1.2(10) . . . . ?
F2 C13 C14 C15 -177.6(6) . . . . ?
C12 C13 C14 C15 0.6(11) . . . . ?
F2 C13 C14 F3 -1.0(10) . . . . ?
C12 C13 C14 F3 177.1(6) . . . . ?
F3 C14 C15 F4 2.2(10) . . . . ?
C13 C14 C15 F4 178.6(6) . . . . ?
F3 C14 C15 C16 -177.4(6) . . . . ?
C13 C14 C15 C16 -1.0(11) . . . . ?
C12 C11 C16 F5 -177.1(6) . . . . ?
C17 C11 C16 F5 4.3(9) . . . . ?
C12 C11 C16 C15 2.0(9) . . . . ?
C17 C11 C16 C15 -176.6(6) . . . . ?
C14 C15 C16 F5 178.8(6) . . . . ?
F4 C15 C16 F5 -0.8(9) . . . . ?
C14 C15 C16 C11 -0.4(10) . . . . ?
F4 C15 C16 C11 -180.0(6) . . . . ?
S1 N1 C17 C7 -164.9(4) . . . . ?
S1 N1 C17 C11 68.5(6) . . . . ?
C8 C7 C17 N1 57.6(7) . . . . ?
P1 C7 C17 N1 175.7(4) . . . . ?
C8 C7 C17 C11 -175.5(5) . . . . ?
P1 C7 C17 C11 -57.3(7) . . . . ?
C16 C11 C17 N1 -111.7(6) . . . . ?
C12 C11 C17 N1 69.8(8) . . . . ?
C16 C11 C17 C7 123.8(6) . . . . ?
C12 C11 C17 C7 -54.7(8) . . . . ?
O1 S1 C18 C21 -57.4(6) . . . . ?
N1 S1 C18 C21 56.6(6) . . . . ?
O1 S1 C18 C19 -179.9(5) . . . . ?
N1 S1 C18 C19 -65.9(6) . . . . ?
O1 S1 C18 C20 61.9(6) . . . . ?
N1 S1 C18 C20 175.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.075
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_148
_database_code_depnum_ccdc_archive 'CCDC 1819865'
loop_
_audit_author_name
_audit_author_address
'Junliang Zhang' 'East China Normal University'
_audit_update_record             
;
2018-01-27 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 F N O4'
_chemical_formula_sum            'C22 H24 F N O4'
_chemical_formula_weight         385.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4515(2)
_cell_length_b                   13.8216(2)
_cell_length_c                   13.0859(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.239(2)
_cell_angle_gamma                90
_cell_volume                     2062.56(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8540
_cell_measurement_theta_min      3.9000
_shelx_estimated_absorpt_T_max   0.858
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            46251
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.043
_diffrn_reflns_theta_max         67.043
_diffrn_reflns_theta_min         3.876
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00 -13.00   1.00    1.00    --    0.00 -51.00 -94.00   30
  2  ω    -19.00  86.00   1.00    1.00    --    0.00  51.00  52.00  105
  3  ω    105.00 131.00   1.00    2.00    --   95.80  51.00  52.00   26
  4  ω     72.00 111.00   1.00    2.00    --   95.80 -51.00 -94.00   39
  5  ω    -11.00  15.00   1.00    1.00    --    0.00  77.00-150.00   26
  6  ω     29.00  62.00   1.00    1.00    --    0.00  19.00  60.00   33
  7  ω     25.00  89.00   1.00    1.00    --    0.00  38.00 -30.00   64
  8  ω     23.00  89.00   1.00    1.00    --    0.00  77.00-150.00   66
  9  ω    -21.00   9.00   1.00    1.00    --    0.00  19.00  60.00   30
 10  ω    -31.00  82.00   1.00    1.00    --    0.00  82.00 -90.00  113
 11  ω    -22.00  47.00   1.00    1.00    --    0.00  57.00-150.00   69
 12  ω    -15.00  11.00   1.00    1.00    --    0.00  38.00 -30.00   26
 13  ω    -19.00  66.00   1.00    1.00    --    0.00  38.00 150.00   85
 14  ω     63.00  95.00   1.00    2.00    --   95.80  82.00 -60.00   32
 15  ω     63.00  93.00   1.00    2.00    --   95.80  82.00 -90.00   30
 16  ω     98.00 124.00   1.00    2.00    --   95.80  82.00 150.00   26
 17  ω    150.00 183.00   1.00    2.00    --   95.80  82.00 -90.00   33
 18  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 19  ω     29.00 122.00   1.00    2.00    --   95.80 -82.00  90.00   93
 20  ω    160.00 185.00   1.00    2.00    --   95.80  82.00-120.00   25
 21  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 150.00   26
 22  ω     75.00 184.00   1.00    2.00    --   95.80  45.00 -30.00  109
 23  ω     63.00  88.00   1.00    2.00    --   95.80  82.00  30.00   25
 24  ω     65.00  90.00   1.00    2.00    --   95.80  77.00   0.00   25
 25  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 137.19   26
 26  ω     67.00  92.00   1.00    2.00    --   95.80  71.00  22.06   25
 27  ω    143.00 185.00   1.00    2.00    --   95.80  71.00  22.06   42
 28  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-155.48   25
 29  ω    127.00 171.00   1.00    2.00    --   95.80  77.00-155.48   44
 30  ω     71.00  98.00   1.00    2.00    --   95.80  58.00 134.64   27
 31  ω     68.00  96.00   1.00    2.00    --   95.80  68.00  66.08   28
 32  ω      6.00 126.00   1.00    2.00    --   95.80 -77.00 150.00  120
 33  ω     75.00 109.00   1.00    2.00    --   95.80  45.00 -60.00   34
 34  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 35  ω    159.00 185.00   1.00    2.00    --   95.80  77.00 -30.00   26
 36  ω     67.00 184.00   1.00    2.00    --   95.80  72.00  73.82  117
 37  ω     65.00  99.00   1.00    2.00    --   95.80  77.00  30.00   34
 38  ω    159.00 185.00   1.00    2.00    --   95.80  77.00 -60.00   26
 39  ω     71.00 184.00   1.00    2.00    --   95.80  60.00-109.45  113
 40  ω    120.00 180.00   1.00    2.00    --   95.80  82.00-180.00   60
 41  ω     73.00 184.00   1.00    2.00    --   95.80  52.00  -5.92  111
 42  ω     76.00 153.00   1.00    2.00    --   95.80  45.00 121.25   77
 43  ω     71.00 185.00   1.00    2.00    --   95.80  61.00 139.59  114
 44  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-120.00   25
 45  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 46  ω     75.00 107.00   1.00    2.00    --   95.80  45.00-180.00   32
 47  ω     75.00 185.00   1.00    2.00    --   95.80  45.00-141.30  110
 48  ω     72.00  98.00   1.00    2.00    --   95.80  61.00-180.00   26
 49  ω     65.00  90.00   1.00    2.00    --   95.80  76.00  24.07   25
 50  ω     63.00  89.00   1.00    2.00    --   95.80  81.00  42.42   26
 51  ω     65.00 126.00   1.00    2.00    --   95.80  77.00-150.00   61
 52  ω     63.00  88.00   1.00    2.00    --   95.80  82.00 -30.00   25
 53  ω     75.00 177.00   1.00    2.00    --   95.80  45.00  30.00  102
 54  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
 55  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-150.00   25
 56  ω     15.00 128.00   1.00    2.00    --   95.80 -82.00 -60.00  113
 57  ω     63.00  88.00   1.00    2.00    --   95.80  82.00 120.00   25
 58  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 59  ω     22.00 123.00   1.00    2.00    --   95.80 -82.00-120.00  101
 60  ω     18.00 128.00   1.00    2.00    --   95.80 -82.00   0.00  110
 61  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-180.00   25
 62  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -30.00   26
 63  ω    123.00 148.00   1.00    2.00    --   95.80  82.00-120.00   25
 64  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0204071000
_diffrn_orient_matrix_UB_12      -0.0643684000
_diffrn_orient_matrix_UB_13      0.0960446000
_diffrn_orient_matrix_UB_21      0.1317049000
_diffrn_orient_matrix_UB_22      0.0247536000
_diffrn_orient_matrix_UB_23      0.0077115000
_diffrn_orient_matrix_UB_31      -0.0222287000
_diffrn_orient_matrix_UB_32      0.0875542000
_diffrn_orient_matrix_UB_33      0.0684713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3315
_reflns_number_total             3604
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.706
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0070(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.1146
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1470P)²+3.7850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3172
_refine_ls_wR_factor_ref         0.3195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C19
 1.52 with sigma of 0.01
3. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C19 \\sim C20: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C19(H19A,H19B)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8980(3) 0.1754(3) 0.2035(3) 0.1105(14) Uani 1 1 d . . . . .
O1 O 0.3188(3) 0.2968(3) 0.8008(3) 0.0790(11) Uani 1 1 d . . . . .
O2 O 0.0891(4) 0.2770(3) 0.5021(3) 0.0913(13) Uani 1 1 d . . . . .
O3 O 0.5607(4) 0.3792(3) 0.4522(5) 0.1085(18) Uani 1 1 d . . . . .
O4 O 0.5573(3) 0.2207(2) 0.4674(3) 0.0618(9) Uani 1 1 d . . . . .
N1 N 0.2042(3) 0.3123(3) 0.6498(3) 0.0512(9) Uani 1 1 d . . . . .
C1 C 0.2410(4) 0.2666(3) 0.7418(3) 0.0542(11) Uani 1 1 d . . . . .
C2 C 0.1708(4) 0.1740(4) 0.7500(4) 0.0609(12) Uani 1 1 d . . . . .
H2 H 0.119579 0.179895 0.805673 0.073 Uiso 1 1 calc R . . . .
C3 C 0.2560(5) 0.0888(4) 0.7717(4) 0.0696(13) Uani 1 1 d . . . . .
H3A H 0.313160 0.105137 0.828365 0.083 Uiso 1 1 calc R . . . .
H3B H 0.212894 0.032334 0.791124 0.083 Uiso 1 1 calc R . . . .
C4 C 0.3178(4) 0.0660(3) 0.6790(4) 0.0632(12) Uani 1 1 d . . . . .
C5 C 0.2550(5) 0.0590(3) 0.5898(4) 0.0655(13) Uani 1 1 d . . . . .
C6 C 0.1262(5) 0.0745(4) 0.5884(4) 0.0745(15) Uani 1 1 d . . . . .
H6A H 0.091003 0.018889 0.618782 0.089 Uiso 1 1 calc R . . . .
H6B H 0.092620 0.080026 0.517914 0.089 Uiso 1 1 calc R . . . .
C7 C 0.0972(4) 0.1663(4) 0.6477(4) 0.0605(12) Uani 1 1 d . . . . .
H7 H 0.013853 0.166187 0.659229 0.073 Uiso 1 1 calc R . . . .
C8 C 0.1252(4) 0.2558(4) 0.5891(4) 0.0594(11) Uani 1 1 d . . . . .
C9 C 0.2534(5) 0.4033(3) 0.6166(5) 0.0707(14) Uani 1 1 d D U . . .
H9 H 0.196561 0.420680 0.558946 0.085 Uiso 1 1 calc R . . . .
C10 C 0.3615(4) 0.3900(3) 0.5636(3) 0.0546(11) Uani 1 1 d . . . . .
H10 H 0.398291 0.446285 0.544309 0.066 Uiso 1 1 calc R . . . .
C11 C 0.4113(4) 0.3081(3) 0.5407(3) 0.0515(10) Uani 1 1 d . . . . .
H11 H 0.380600 0.249430 0.560430 0.062 Uiso 1 1 calc R . . . .
C12 C 0.5162(4) 0.3103(3) 0.4834(4) 0.0554(11) Uani 1 1 d . . . . .
C13 C 0.6466(4) 0.2131(3) 0.3996(4) 0.0525(10) Uani 1 1 d . . . . .
C14 C 0.7625(4) 0.2226(4) 0.4364(4) 0.0689(13) Uani 1 1 d . . . . .
H14 H 0.783151 0.237162 0.505067 0.083 Uiso 1 1 calc R . . . .
C15 C 0.8473(4) 0.2102(4) 0.3691(5) 0.0769(15) Uani 1 1 d . . . . .
H15 H 0.926281 0.216579 0.391716 0.092 Uiso 1 1 calc R . . . .
C16 C 0.8139(4) 0.1883(4) 0.2694(5) 0.0694(14) Uani 1 1 d . . . . .
C17 C 0.6998(5) 0.1808(4) 0.2323(4) 0.0719(14) Uani 1 1 d . . . . .
H17 H 0.679575 0.168017 0.163185 0.086 Uiso 1 1 calc R . . . .
C18 C 0.6143(4) 0.1925(4) 0.2991(4) 0.0632(12) Uani 1 1 d . . . . .
H18 H 0.535437 0.186296 0.275826 0.076 Uiso 1 1 calc R . . . .
C19 C 0.2427(8) 0.4873(6) 0.6863(8) 0.128(3) Uani 1 1 d D U . . .
H19A H 0.283332 0.542978 0.661678 0.154 Uiso 1 1 calc R . . . .
H19B H 0.276807 0.471789 0.754937 0.154 Uiso 1 1 calc R . . . .
C20 C 0.1051(9) 0.5104(7) 0.6876(10) 0.155(4) Uani 1 1 d . U . . .
H20A H 0.069029 0.512494 0.618515 0.233 Uiso 1 1 calc GR . . . .
H20B H 0.095404 0.571805 0.720117 0.233 Uiso 1 1 calc GR . . . .
H20C H 0.068811 0.460728 0.725092 0.233 Uiso 1 1 calc GR . . . .
C21 C 0.3038(8) 0.0351(5) 0.4914(5) 0.104(2) Uani 1 1 d . . . . .
H21A H 0.297903 0.090649 0.447193 0.156 Uiso 1 1 calc GR . . . .
H21B H 0.260419 -0.017593 0.458826 0.156 Uiso 1 1 calc GR . . . .
H21C H 0.384668 0.016911 0.504809 0.156 Uiso 1 1 calc GR . . . .
C22 C 0.4491(6) 0.0566(5) 0.6940(7) 0.105(2) Uani 1 1 d . . . . .
H22A H 0.482969 0.118283 0.713141 0.158 Uiso 1 1 calc GR . . . .
H22B H 0.477986 0.035236 0.631264 0.158 Uiso 1 1 calc GR . . . .
H22C H 0.470035 0.010396 0.747314 0.158 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.362(6) . ?
O1 C1 1.200(5) . ?
O2 C8 1.211(6) . ?
O3 C12 1.171(6) . ?
O4 C12 1.348(5) . ?
O4 C13 1.417(5) . ?
N1 C1 1.390(6) . ?
N1 C8 1.389(6) . ?
N1 C9 1.460(6) . ?
C1 C2 1.520(6) . ?
C2 H2 0.9800 . ?
C2 C3 1.539(7) . ?
C2 C7 1.519(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.492(7) . ?
C4 C5 1.317(8) . ?
C4 C22 1.504(8) . ?
C5 C6 1.488(8) . ?
C5 C21 1.487(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.539(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.506(7) . ?
C9 H9 0.9800 . ?
C9 C10 1.485(6) . ?
C9 C19 1.489(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.314(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.473(6) . ?
C13 C14 1.376(7) . ?
C13 C18 1.363(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(8) . ?
C16 C17 1.355(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(7) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.609(13) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O4 C13 116.6(3) . . ?
C1 N1 C9 123.7(4) . . ?
C8 N1 C1 111.7(4) . . ?
C8 N1 C9 124.2(4) . . ?
O1 C1 N1 123.2(4) . . ?
O1 C1 C2 127.9(5) . . ?
N1 C1 C2 108.9(4) . . ?
C1 C2 H2 109.8 . . ?
C1 C2 C3 109.1(4) . . ?
C3 C2 H2 109.8 . . ?
C7 C2 C1 104.6(4) . . ?
C7 C2 H2 109.8 . . ?
C7 C2 C3 113.6(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.6(4) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 C22 117.0(5) . . ?
C5 C4 C3 118.3(5) . . ?
C5 C4 C22 124.6(6) . . ?
C4 C5 C6 117.4(5) . . ?
C4 C5 C21 124.4(6) . . ?
C21 C5 C6 118.2(6) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.8(4) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C2 C7 C6 112.0(4) . . ?
C2 C7 H7 109.6 . . ?
C6 C7 H7 109.6 . . ?
C8 C7 C2 105.3(4) . . ?
C8 C7 C6 110.8(4) . . ?
C8 C7 H7 109.6 . . ?
O2 C8 N1 123.4(5) . . ?
O2 C8 C7 127.4(4) . . ?
N1 C8 C7 109.2(4) . . ?
N1 C9 H9 101.2 . . ?
N1 C9 C10 113.2(4) . . ?
N1 C9 C19 115.7(5) . . ?
C10 C9 H9 101.2 . . ?
C10 C9 C19 120.1(5) . . ?
C19 C9 H9 101.2 . . ?
C9 C10 H10 116.2 . . ?
C11 C10 C9 127.6(4) . . ?
C11 C10 H10 116.2 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(4) . . ?
C12 C11 H11 120.4 . . ?
O3 C12 O4 121.5(4) . . ?
O3 C12 C11 126.6(4) . . ?
O4 C12 C11 111.9(3) . . ?
C14 C13 O4 120.1(4) . . ?
C18 C13 O4 118.1(4) . . ?
C18 C13 C14 121.7(4) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.5(5) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 F1 118.9(5) . . ?
C17 C16 F1 118.5(6) . . ?
C17 C16 C15 122.5(5) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(5) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 119.3(5) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C9 C19 H19A 110.3 . . ?
C9 C19 H19B 110.3 . . ?
C9 C19 C20 107.3(7) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.269
_oxdiff_exptl_absorpt_empirical_full_min 0.481
